Host-group-containing polymerizable monomer, polymer material, method for producing same, and clathrate compound and method for producing same

Abstract

Provided are a host-group-containing polymerizable monomer usable as a starting material for producing a macromolecular material with a high degree of freedom in material design, and excellent toughness and strength; a macromolecular material produced using the host-group-containing polymerizable monomer; and a method for producing the macromolecular material. The host-group-containing polymerizable monomer according to the present invention is a host-group-containing polymerizable monomer, and the host group is a monovalent group formed by removing one hydrogen atom or hydroxy group from a cyclodextrin derivative. The cyclodextrin derivative has such a structure that the hydrogen atom of at least one hydroxy group of a cyclodextrin is replaced with a group selected from the group consisting of a hydrocarbon group, an acyl group, and —CONHR wherein R represents a methyl group or an ethyl group.

The invention claimed is: 
     
       1. A host-group-containing polymerizable monomer,
 the host group being a monovalent group formed by removing one hydrogen atom or hydroxy group from a cyclodextrin derivative, 
 the cyclodextrin derivative having such a structure that a hydrogen atom of at least one hydroxy group of a cyclodextrin is replaced with a group selected from the group consisting of a hydrocarbon group, an acyl group, and —CONHR wherein R represents a methyl group or an ethyl group, 
 the host group being a functional group capable of having a host-guest interaction with a guest group, the host group not clathrating a guest-group-containing polymer, 
 the cyclodextrin being at least one member selected from the group consisting of α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin. 
 
     
     
       2. The host-group-containing polymerizable monomer according to  claim 1 , wherein the acyl group is an acetyl group. 
     
     
       3. The host-group-containing polymerizable monomer according to  claim 1 , wherein the hydrocarbon group has 1 to 4 carbon atoms. 
     
     
       4. The host-group-containing polymerizable monomer according to  claim 1 , which is represented by the following formula (h1): 
       
         
           
           
               
               
           
         
         wherein Ra represents a hydrogen atom or a methyl group, R H  represents the host group, and R 1  represents a divalent group formed by removing one hydrogen atom from a monovalent group selected from the group consisting of a hydroxy group, a thiol group, an alkoxy group optionally having at least one substituent, an thioalkoxy group optionally having at least one substituent, an alkyl group optionally having at least one substituent, an amino group optionally having one substituent, an amide group optionally having one substituent, an aldehyde group, and a carboxy group. 
       
     
     
       5. The host-group-containing polymerizable monomer according to  claim 1 , which is represented by the following formula (h2): 
       
         
           
           
               
               
           
         
         wherein Ra represents a hydrogen atom or a methyl group, R H  represents the host group, and R 1  represents a divalent group formed by removing one hydrogen atom from a monovalent group selected from the group consisting of a hydroxy group, a thiol group, an alkoxy group optionally having at least one substituent, an thioalkoxy group optionally having at least one substituent, an alkyl group optionally having at least one substituent, an amino group optionally having one substituent, an amide group optionally having one substituent, an aldehyde group, and a carboxy group. 
       
     
     
       6. The host-group-containing polymerizable monomer according to  claim 1 , which is represented by the following formula (h40):
   R 40 -R H   (h40)
 
 wherein R 40  represents NH 2  or OH, and R H  represents the host group. 
 
     
     
       7. A macromolecular material comprising a polymer of a polymerizable monomer mixture containing the host-group-containing polymerizable monomer of  claim 1 . 
     
     
       8. The macromolecular material according to  claim 7 , wherein the polymerizable monomer mixture contains a polymerizable monomer of a size that can penetrate the host group of the host-group-containing polymerizable monomer. 
     
     
       9. The macromolecular material according to  claim 7 , further comprising a polymer that has a guest group capable of having a host-guest interaction with the host group. 
     
     
       10. A clathrate compound comprising the host-group-containing polymerizable monomer of  claim 1  and a guest-group-containing polymerizable monomer. 
     
     
       11. A clathrate compound comprising the host-group-containing polymerizable monomer of  claim 6  and a compound having a functional group capable of undergoing a condensation reaction. 
     
     
       12. A macromolecular material comprising a polymer of a polymerizable monomer containing the clathrate compound of  claim 10 . 
     
     
       13. A method for producing a macromolecular material,
 the method comprising performing polymerization of a polymerizable monomer mixture containing the host-group-containing polymerizable monomer of  claim 1  to obtain a polymer. 
 
     
     
       14. The method for producing a macromolecular material according to  claim 13 , wherein the polymerization is performed in the absence of a solvent. 
     
     
       15. A method for producing the clathrate compound of  claim 10 , the method comprising mixing the host-group-containing polymerizable monomer and the guest-group-containing polymerizable monomer to obtain the clathrate compound. 
     
     
       16. The host-group-containing polymerizable monomer according to  claim 2 , wherein the hydrocarbon group has 1 to 4 carbon atoms. 
     
     
       17. The host-group-containing polymerizable monomer according to  claim 2 , which is represented by the following formula (h1): 
       
         
           
           
               
               
           
         
         wherein Ra represents a hydrogen atom or a methyl group, R H  represents the host group, and R 1  represents a divalent group formed by removing one hydrogen atom from a monovalent group selected from the group consisting of a hydroxy group, a thiol group, an alkoxy group optionally having at least one substituent, an thioalkoxy group optionally having at least one substituent, an alkyl group optionally having at least one substituent, an amino group optionally having one substituent, an amide group optionally having one substituent, an aldehyde group, and a carboxy group. 
       
     
     
       18. The host-group-containing polymerizable monomer according to  claim 2 , which is represented by the following formula (h2): 
       
         
           
           
               
               
           
         
         wherein Ra represents a hydrogen atom or a methyl group, R H  represents the host group, and R 1  represents a divalent group formed by removing one hydrogen atom from a monovalent group selected from the group consisting of a hydroxy group, a thiol group, an alkoxy group optionally having at least one substituent, an thioalkoxy group optionally having at least one substituent, an alkyl group optionally having at least one substituent, an amino group optionally having one substituent, an amide group optionally having one substituent, an aldehyde group, and a carboxy group. 
       
     
     
       19. The host-group-containing polymerizable monomer according to  claim 2 , which is represented by the following formula (h40):
   R 40 -R H   (h40)
 
 wherein R 40  represents NH 2  or OH, and R H  represents the host group. 
 
     
     
       20. A macromolecular material comprising a polymer of a polymerizable monomer mixture containing the host-group-containing polymerizable monomer of  claim 2 .